HRP20151423T1 - DERIVATI [1,2,3]TRIAZOLO[4,5-d]PIRIMIDINA KAO AGONISTI RECEPTORA KANABINOIDA 2 - Google Patents
DERIVATI [1,2,3]TRIAZOLO[4,5-d]PIRIMIDINA KAO AGONISTI RECEPTORA KANABINOIDA 2 Download PDFInfo
- Publication number
- HRP20151423T1 HRP20151423T1 HRP20151423TT HRP20151423T HRP20151423T1 HR P20151423 T1 HRP20151423 T1 HR P20151423T1 HR P20151423T T HRP20151423T T HR P20151423TT HR P20151423 T HRP20151423 T HR P20151423T HR P20151423 T1 HRP20151423 T1 HR P20151423T1
- Authority
- HR
- Croatia
- Prior art keywords
- triazolo
- pyrrolidin
- tert
- butyl
- pyrimidine
- Prior art date
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- 239000000556 agonist Substances 0.000 title 2
- GIIGHSIIKVOWKZ-UHFFFAOYSA-N 2h-triazolo[4,5-d]pyrimidine Chemical class N1=CN=CC2=NNN=C21 GIIGHSIIKVOWKZ-UHFFFAOYSA-N 0.000 title 1
- 102100036214 Cannabinoid receptor 2 Human genes 0.000 title 1
- 101710187022 Cannabinoid receptor 2 Proteins 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 19
- -1 haloalkylphenyl Chemical group 0.000 claims 16
- 125000000217 alkyl group Chemical group 0.000 claims 9
- 125000000623 heterocyclic group Chemical group 0.000 claims 9
- 125000003545 alkoxy group Chemical group 0.000 claims 6
- 125000001188 haloalkyl group Chemical group 0.000 claims 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 6
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000004802 cyanophenyl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
- 229910052757 nitrogen Inorganic materials 0.000 claims 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 4
- 125000004076 pyridyl group Chemical group 0.000 claims 4
- 125000005036 alkoxyphenyl group Chemical group 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 125000006485 halo alkoxy phenyl group Chemical group 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 150000002367 halogens Chemical class 0.000 claims 3
- 125000005059 halophenyl group Chemical group 0.000 claims 3
- 125000002757 morpholinyl group Chemical group 0.000 claims 3
- XZEIKNPDGSWHEB-ZDUSSCGKSA-N (3s)-1-[5-tert-butyl-2-[[2-(trifluoromethyl)phenyl]methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)C(F)(F)F)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 XZEIKNPDGSWHEB-ZDUSSCGKSA-N 0.000 claims 2
- FYSUYVSHNBXDSD-UHFFFAOYSA-N 2-[(2-bromophenyl)methyl]-5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC=CC=3)Br)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 FYSUYVSHNBXDSD-UHFFFAOYSA-N 0.000 claims 2
- VWQHXMLRTYNZIM-UHFFFAOYSA-N 2-[[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]methyl]benzonitrile Chemical compound C12=NN(CC=3C(=CC=CC=3)C#N)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 VWQHXMLRTYNZIM-UHFFFAOYSA-N 0.000 claims 2
- ZOUYCQHMLWVXDT-UHFFFAOYSA-N 3-[[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]methyl]-4-methyl-1,2,5-oxadiazole Chemical compound CC1=NON=C1CN1N=C2C(N3CC(F)(F)CC3)=NC(C(C)(C)C)=NC2=N1 ZOUYCQHMLWVXDT-UHFFFAOYSA-N 0.000 claims 2
- KECTXODKMCMGSY-UHFFFAOYSA-N 4-[5-tert-butyl-2-[(2-chlorophenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]morpholine Chemical compound C12=NN(CC=3C(=CC=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCOCC1 KECTXODKMCMGSY-UHFFFAOYSA-N 0.000 claims 2
- DHRQVVUYHYCSKZ-UHFFFAOYSA-N 5-tert-butyl-2-(cyclohexylmethyl)-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC3CCCCC3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 DHRQVVUYHYCSKZ-UHFFFAOYSA-N 0.000 claims 2
- PJUQAFGQTRRVMU-GFCCVEGCSA-N 5-tert-butyl-2-[(1r)-1-(2-chlorophenyl)ethyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C1([C@@H](C)N2N=C3C(N4CC(F)(F)CC4)=NC(=NC3=N2)C(C)(C)C)=CC=CC=C1Cl PJUQAFGQTRRVMU-GFCCVEGCSA-N 0.000 claims 2
- NWQPKTYZUOBLJX-UHFFFAOYSA-N 5-tert-butyl-2-[(3-chloropyridin-2-yl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC=CN=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 NWQPKTYZUOBLJX-UHFFFAOYSA-N 0.000 claims 2
- TXKMOXBZSZKEJA-UHFFFAOYSA-N 5-tert-butyl-2-[(3-chloropyridin-4-yl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CN=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 TXKMOXBZSZKEJA-UHFFFAOYSA-N 0.000 claims 2
- AHAMWCYDFJMDNB-UHFFFAOYSA-N 5-tert-butyl-2-[(4-chloropyridin-3-yl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC=NC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 AHAMWCYDFJMDNB-UHFFFAOYSA-N 0.000 claims 2
- QSRNVFRWHSSQNS-UHFFFAOYSA-N 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-2-(2,2,2-trifluoroethyl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC(F)(F)F)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 QSRNVFRWHSSQNS-UHFFFAOYSA-N 0.000 claims 2
- VFTMGSUKNOXTHO-UHFFFAOYSA-N 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-2-(2-phenylethyl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CCC=3C=CC=CC=3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 VFTMGSUKNOXTHO-UHFFFAOYSA-N 0.000 claims 2
- VJWKMAMXVIMMCF-UHFFFAOYSA-N 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-2-(pyridin-4-ylmethyl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C=CN=CC=3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 VJWKMAMXVIMMCF-UHFFFAOYSA-N 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims 2
- 230000000735 allogeneic effect Effects 0.000 claims 2
- 208000019425 cirrhosis of liver Diseases 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims 2
- 125000003838 furazanyl group Chemical group 0.000 claims 2
- 125000005216 haloheteroaryl group Chemical group 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- YIMBODSNLPVSIP-OAHLLOKOSA-N (3r)-1-[5-tert-butyl-2-(3,3,3-trifluoropropyl)triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CCC(F)(F)F)N=C2N=C(C(C)(C)C)N=C1N1CC[C@@](C)(O)C1 YIMBODSNLPVSIP-OAHLLOKOSA-N 0.000 claims 1
- AGGOQQSMHUVELT-GOSISDBHSA-N (3r)-1-[5-tert-butyl-2-[(1-cyclopropyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3N(N=NN=3)C3CC3)N=C2N=C(C(C)(C)C)N=C1N1CC[C@@](C)(O)C1 AGGOQQSMHUVELT-GOSISDBHSA-N 0.000 claims 1
- TVAZUSIVGZGCAZ-MRXNPFEDSA-N (3r)-1-[5-tert-butyl-2-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1N=C2C(N3C[C@](C)(O)CC3)=NC(C(C)(C)C)=NC2=N1 TVAZUSIVGZGCAZ-MRXNPFEDSA-N 0.000 claims 1
- HVYYKTYVYHOMLY-SECBINFHSA-N (3r)-1-[5-tert-butyl-2-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1N=C2C(N3C[C@H](O)CC3)=NC(C(C)(C)C)=NC2=N1 HVYYKTYVYHOMLY-SECBINFHSA-N 0.000 claims 1
- DSRLAHZUYCYAMV-HXUWFJFHSA-N (3r)-1-[5-tert-butyl-2-[(2-chlorophenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@@](C)(O)C1 DSRLAHZUYCYAMV-HXUWFJFHSA-N 0.000 claims 1
- UZBKRADQIKOOTQ-OAQYLSRUSA-N (3r)-1-[5-tert-butyl-2-[(2-methylsulfonylphenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)S(C)(=O)=O)N=C2N=C(C(C)(C)C)N=C1N1CC[C@@](C)(O)C1 UZBKRADQIKOOTQ-OAQYLSRUSA-N 0.000 claims 1
- QRJBCNUOFPSONQ-LJQANCHMSA-N (3r)-1-[5-tert-butyl-2-[(3-chloropyridin-2-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CN=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@@](C)(O)C1 QRJBCNUOFPSONQ-LJQANCHMSA-N 0.000 claims 1
- NBLVYBCKKMPIBL-QGZVFWFLSA-N (3r)-1-[5-tert-butyl-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound CC1=NOC(CN2N=C3C(N4C[C@](C)(O)CC4)=NC(=NC3=N2)C(C)(C)C)=N1 NBLVYBCKKMPIBL-QGZVFWFLSA-N 0.000 claims 1
- NMTROVMJLSMPAI-QGZVFWFLSA-N (3r)-1-[5-tert-butyl-2-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound CC1=NON=C1CN1N=C2C(N3C[C@](C)(O)CC3)=NC(C(C)(C)C)=NC2=N1 NMTROVMJLSMPAI-QGZVFWFLSA-N 0.000 claims 1
- MMTFJOHDVWTWQY-QGZVFWFLSA-N (3r)-1-[5-tert-butyl-2-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound O1C(C)=NN=C1CN1N=C2C(N3C[C@](C)(O)CC3)=NC(C(C)(C)C)=NC2=N1 MMTFJOHDVWTWQY-QGZVFWFLSA-N 0.000 claims 1
- WSKCTPGFWGPLMS-HXUWFJFHSA-N (3r)-1-[5-tert-butyl-2-[[2-(trifluoromethyl)phenyl]methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)C(F)(F)F)N=C2N=C(C(C)(C)C)N=C1N1CC[C@@](C)(O)C1 WSKCTPGFWGPLMS-HXUWFJFHSA-N 0.000 claims 1
- IFVVNGFAEPPWCK-NSHDSACASA-N (3s)-1-[2-[(2-chlorophenyl)methyl]-5-(2,2,2-trifluoroethoxy)triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1C(C1=N2)=NC(OCC(F)(F)F)=NC1=NN2CC1=CC=CC=C1Cl IFVVNGFAEPPWCK-NSHDSACASA-N 0.000 claims 1
- JVSYCEMCGWZHHT-ZDUSSCGKSA-N (3s)-1-[2-[(2-chlorophenyl)methyl]-5-propan-2-yloxytriazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)Cl)N=C2N=C(OC(C)C)N=C1N1CC[C@H](O)C1 JVSYCEMCGWZHHT-ZDUSSCGKSA-N 0.000 claims 1
- LYPULYSGFPXDHH-NSHDSACASA-N (3s)-1-[5-(2,2,2-trifluoroethoxy)-2-[[2-(trifluoromethyl)phenyl]methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C1[C@@H](O)CCN1C(C1=N2)=NC(OCC(F)(F)F)=NC1=NN2CC1=CC=CC=C1C(F)(F)F LYPULYSGFPXDHH-NSHDSACASA-N 0.000 claims 1
- UTIADVPEIFDKEK-VIFPVBQESA-N (3s)-1-[5-(tert-butylamino)-2-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1N=C2C(N3C[C@@H](O)CC3)=NC(NC(C)(C)C)=NC2=N1 UTIADVPEIFDKEK-VIFPVBQESA-N 0.000 claims 1
- YIMBODSNLPVSIP-HNNXBMFYSA-N (3s)-1-[5-tert-butyl-2-(3,3,3-trifluoropropyl)triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CCC(F)(F)F)N=C2N=C(C(C)(C)C)N=C1N1CC[C@](C)(O)C1 YIMBODSNLPVSIP-HNNXBMFYSA-N 0.000 claims 1
- AGGOQQSMHUVELT-SFHVURJKSA-N (3s)-1-[5-tert-butyl-2-[(1-cyclopropyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3N(N=NN=3)C3CC3)N=C2N=C(C(C)(C)C)N=C1N1CC[C@](C)(O)C1 AGGOQQSMHUVELT-SFHVURJKSA-N 0.000 claims 1
- JQHLTHYIYAZTRT-NSHDSACASA-N (3s)-1-[5-tert-butyl-2-[(1-cyclopropyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3N(N=NN=3)C3CC3)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 JQHLTHYIYAZTRT-NSHDSACASA-N 0.000 claims 1
- TVAZUSIVGZGCAZ-INIZCTEOSA-N (3s)-1-[5-tert-butyl-2-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1N=C2C(N3C[C@@](C)(O)CC3)=NC(C(C)(C)C)=NC2=N1 TVAZUSIVGZGCAZ-INIZCTEOSA-N 0.000 claims 1
- HVYYKTYVYHOMLY-VIFPVBQESA-N (3s)-1-[5-tert-butyl-2-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1N=C2C(N3C[C@@H](O)CC3)=NC(C(C)(C)C)=NC2=N1 HVYYKTYVYHOMLY-VIFPVBQESA-N 0.000 claims 1
- LNSGQUHVXUOWGI-LBPRGKRZSA-N (3s)-1-[5-tert-butyl-2-[(2,3-dichlorophenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=C(Cl)C=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 LNSGQUHVXUOWGI-LBPRGKRZSA-N 0.000 claims 1
- FYMPUTMBZGPBGP-NSHDSACASA-N (3s)-1-[5-tert-butyl-2-[(2,5-dimethyl-1,2,4-triazol-3-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=C(C)N=C1CN1N=C2C(N3C[C@@H](O)CC3)=NC(C(C)(C)C)=NC2=N1 FYMPUTMBZGPBGP-NSHDSACASA-N 0.000 claims 1
- BIAYIFRVBUURNA-ZDUSSCGKSA-N (3s)-1-[5-tert-butyl-2-[(2,5-dimethylpyrazol-3-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=C(C)C=C1CN1N=C2C(N3C[C@@H](O)CC3)=NC(C(C)(C)C)=NC2=N1 BIAYIFRVBUURNA-ZDUSSCGKSA-N 0.000 claims 1
- DSRLAHZUYCYAMV-FQEVSTJZSA-N (3s)-1-[5-tert-butyl-2-[(2-chlorophenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@](C)(O)C1 DSRLAHZUYCYAMV-FQEVSTJZSA-N 0.000 claims 1
- ZUGQZZXSAJGHAL-LBPRGKRZSA-N (3s)-1-[5-tert-butyl-2-[(2-chloropyridin-3-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=NC=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 ZUGQZZXSAJGHAL-LBPRGKRZSA-N 0.000 claims 1
- XRNDLLSCTRPFJY-JTQLQIEISA-N (3s)-1-[5-tert-butyl-2-[(2-methyl-1,2,4-triazol-3-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=CN=C1CN1N=C2C(N3C[C@@H](O)CC3)=NC(C(C)(C)C)=NC2=N1 XRNDLLSCTRPFJY-JTQLQIEISA-N 0.000 claims 1
- UZBKRADQIKOOTQ-NRFANRHFSA-N (3s)-1-[5-tert-butyl-2-[(2-methylsulfonylphenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)S(C)(=O)=O)N=C2N=C(C(C)(C)C)N=C1N1CC[C@](C)(O)C1 UZBKRADQIKOOTQ-NRFANRHFSA-N 0.000 claims 1
- DTQULOTVGBZIAA-AWEZNQCLSA-N (3s)-1-[5-tert-butyl-2-[(2-methylsulfonylphenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)S(C)(=O)=O)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 DTQULOTVGBZIAA-AWEZNQCLSA-N 0.000 claims 1
- AZYJMRNLICUYJY-JTQLQIEISA-N (3s)-1-[5-tert-butyl-2-[(3,4-dichloropyridin-2-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=C(Cl)C=CN=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 AZYJMRNLICUYJY-JTQLQIEISA-N 0.000 claims 1
- YCAJBYGNPSACFS-JTQLQIEISA-N (3s)-1-[5-tert-butyl-2-[(3,6-dichloropyridin-2-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=C(Cl)N=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 YCAJBYGNPSACFS-JTQLQIEISA-N 0.000 claims 1
- QRJBCNUOFPSONQ-IBGZPJMESA-N (3s)-1-[5-tert-butyl-2-[(3-chloropyridin-2-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CN=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@](C)(O)C1 QRJBCNUOFPSONQ-IBGZPJMESA-N 0.000 claims 1
- HGAPLELAEVQSTF-NSHDSACASA-N (3s)-1-[5-tert-butyl-2-[(3-chloropyridin-2-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CN=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 HGAPLELAEVQSTF-NSHDSACASA-N 0.000 claims 1
- NBLVYBCKKMPIBL-KRWDZBQOSA-N (3s)-1-[5-tert-butyl-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound CC1=NOC(CN2N=C3C(N4C[C@@](C)(O)CC4)=NC(=NC3=N2)C(C)(C)C)=N1 NBLVYBCKKMPIBL-KRWDZBQOSA-N 0.000 claims 1
- CSJXDZLGQPJABO-JTQLQIEISA-N (3s)-1-[5-tert-butyl-2-[(3-methyl-1,2,4-oxadiazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CC1=NOC(CN2N=C3C(N4C[C@@H](O)CC4)=NC(=NC3=N2)C(C)(C)C)=N1 CSJXDZLGQPJABO-JTQLQIEISA-N 0.000 claims 1
- WOWZEXZPNQRDFX-NSHDSACASA-N (3s)-1-[5-tert-butyl-2-[(3-methyltriazol-4-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NC=C1CN1N=C2C(N3C[C@@H](O)CC3)=NC(C(C)(C)C)=NC2=N1 WOWZEXZPNQRDFX-NSHDSACASA-N 0.000 claims 1
- NMTROVMJLSMPAI-KRWDZBQOSA-N (3s)-1-[5-tert-butyl-2-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound CC1=NON=C1CN1N=C2C(N3C[C@@](C)(O)CC3)=NC(C(C)(C)C)=NC2=N1 NMTROVMJLSMPAI-KRWDZBQOSA-N 0.000 claims 1
- FVCVERVZGCGKRS-JTQLQIEISA-N (3s)-1-[5-tert-butyl-2-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CC1=NON=C1CN1N=C2C(N3C[C@@H](O)CC3)=NC(C(C)(C)C)=NC2=N1 FVCVERVZGCGKRS-JTQLQIEISA-N 0.000 claims 1
- DQLQPGNZRMPEGZ-JTQLQIEISA-N (3s)-1-[5-tert-butyl-2-[(5-methyl-1,2,4-oxadiazol-3-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound O1C(C)=NC(CN2N=C3C(N4C[C@@H](O)CC4)=NC(=NC3=N2)C(C)(C)C)=N1 DQLQPGNZRMPEGZ-JTQLQIEISA-N 0.000 claims 1
- MMTFJOHDVWTWQY-KRWDZBQOSA-N (3s)-1-[5-tert-butyl-2-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound O1C(C)=NN=C1CN1N=C2C(N3C[C@@](C)(O)CC3)=NC(C(C)(C)C)=NC2=N1 MMTFJOHDVWTWQY-KRWDZBQOSA-N 0.000 claims 1
- IHFOCRSJISWSLC-JTQLQIEISA-N (3s)-1-[5-tert-butyl-2-[(5-methyl-1,3,4-oxadiazol-2-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound O1C(C)=NN=C1CN1N=C2C(N3C[C@@H](O)CC3)=NC(C(C)(C)C)=NC2=N1 IHFOCRSJISWSLC-JTQLQIEISA-N 0.000 claims 1
- WSKCTPGFWGPLMS-FQEVSTJZSA-N (3s)-1-[5-tert-butyl-2-[[2-(trifluoromethyl)phenyl]methyl]triazolo[4,5-d]pyrimidin-7-yl]-3-methylpyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=CC=CC=3)C(F)(F)F)N=C2N=C(C(C)(C)C)N=C1N1CC[C@](C)(O)C1 WSKCTPGFWGPLMS-FQEVSTJZSA-N 0.000 claims 1
- UERPQIBJBHSGLB-AWEZNQCLSA-N (3s)-1-[5-tert-butyl-2-[[2-[(4-nitro-2,1,3-benzoxadiazol-7-yl)amino]pyridin-3-yl]methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound C12=NN(CC=3C(=NC=CC=3)NC=3C4=NON=C4C([N+]([O-])=O)=CC=3)N=C2N=C(C(C)(C)C)N=C1N1CC[C@H](O)C1 UERPQIBJBHSGLB-AWEZNQCLSA-N 0.000 claims 1
- HVYYKTYVYHOMLY-UHFFFAOYSA-N 1-[5-tert-butyl-2-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1N=C2C(N3CC(O)CC3)=NC(C(C)(C)C)=NC2=N1 HVYYKTYVYHOMLY-UHFFFAOYSA-N 0.000 claims 1
- PDDHNWZJVQFDAC-VIFPVBQESA-N 2-[(3-chloropyridin-2-yl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)-5-[(2s)-1,1,1-trifluoropropan-2-yl]oxytriazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC=CN=3)Cl)N=C2N=C(O[C@@H](C)C(F)(F)F)N=C1N1CCC(F)(F)C1 PDDHNWZJVQFDAC-VIFPVBQESA-N 0.000 claims 1
- WYXDIBQJQFCQBO-UHFFFAOYSA-N 2-[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]-1-(2-chlorophenyl)ethanone Chemical compound C12=NN(CC(=O)C=3C(=CC=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 WYXDIBQJQFCQBO-UHFFFAOYSA-N 0.000 claims 1
- WRTMKNFGOCVJDC-UHFFFAOYSA-N 2-[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]-1-(3-chlorophenyl)ethanone Chemical compound C12=NN(CC(=O)C=3C=C(Cl)C=CC=3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 WRTMKNFGOCVJDC-UHFFFAOYSA-N 0.000 claims 1
- BNJYADGGYUVFFQ-UHFFFAOYSA-N 2-[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]-1-(4-chlorophenyl)ethanone Chemical compound C12=NN(CC(=O)C=3C=CC(Cl)=CC=3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 BNJYADGGYUVFFQ-UHFFFAOYSA-N 0.000 claims 1
- WOLSQXADZKFUNV-UHFFFAOYSA-N 2-[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]-1-pyridin-2-ylethanone Chemical compound C12=NN(CC(=O)C=3N=CC=CC=3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 WOLSQXADZKFUNV-UHFFFAOYSA-N 0.000 claims 1
- AWHBIAOCYQVQFB-UHFFFAOYSA-N 2-[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]-1-pyridin-3-ylethanone Chemical compound C12=NN(CC(=O)C=3C=NC=CC=3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 AWHBIAOCYQVQFB-UHFFFAOYSA-N 0.000 claims 1
- MMQYRDGSDOJFOB-UHFFFAOYSA-N 2-[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]ethanol Chemical compound C12=NN(CCO)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 MMQYRDGSDOJFOB-UHFFFAOYSA-N 0.000 claims 1
- PXSVUKSXRQSLMN-UHFFFAOYSA-N 2-[[5-tert-butyl-7-(3,3,4,4-tetrafluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]methyl]-5-methyl-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1CN1N=C2C(N3CC(F)(F)C(F)(F)C3)=NC(C(C)(C)C)=NC2=N1 PXSVUKSXRQSLMN-UHFFFAOYSA-N 0.000 claims 1
- GQTQXPZZDSUHBO-UHFFFAOYSA-N 2-[[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]methyl]-5-methyl-1,3,4-oxadiazole Chemical compound O1C(C)=NN=C1CN1N=C2C(N3CC(F)(F)CC3)=NC(C(C)(C)C)=NC2=N1 GQTQXPZZDSUHBO-UHFFFAOYSA-N 0.000 claims 1
- FPAZFEUMWZYSFU-ZETCQYMHSA-N 2-[[7-(3,3-difluoropyrrolidin-1-yl)-5-[(2s)-1,1,1-trifluoropropan-2-yl]oxytriazolo[4,5-d]pyrimidin-2-yl]methyl]-5-methyl-1,3,4-oxadiazole Chemical compound C12=NN(CC=3OC(C)=NN=3)N=C2N=C(O[C@@H](C)C(F)(F)F)N=C1N1CCC(F)(F)C1 FPAZFEUMWZYSFU-ZETCQYMHSA-N 0.000 claims 1
- QEHZTUUVLJWQNT-UHFFFAOYSA-N 3-[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]thietane 1,1-dioxide Chemical compound C12=NN(C3CS(=O)(=O)C3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 QEHZTUUVLJWQNT-UHFFFAOYSA-N 0.000 claims 1
- UAPMMZKSLSPTAS-UHFFFAOYSA-N 3-[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]thiolane 1,1-dioxide Chemical compound C12=NN(C3CS(=O)(=O)CC3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 UAPMMZKSLSPTAS-UHFFFAOYSA-N 0.000 claims 1
- CSHMGFXNGKEZTN-UHFFFAOYSA-N 3-[[5-tert-butyl-7-(3,3,4,4-tetrafluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]methyl]-4-methyl-1,2,5-oxadiazole Chemical compound CC1=NON=C1CN1N=C2C(N3CC(F)(F)C(F)(F)C3)=NC(C(C)(C)C)=NC2=N1 CSHMGFXNGKEZTN-UHFFFAOYSA-N 0.000 claims 1
- OCHCWMMDHVRGHT-UHFFFAOYSA-N 3-[[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]methyl]-5-chloro-n,n-dimethylpyridin-4-amine Chemical compound CN(C)C1=C(Cl)C=NC=C1CN1N=C2C(N3CC(F)(F)CC3)=NC(C(C)(C)C)=NC2=N1 OCHCWMMDHVRGHT-UHFFFAOYSA-N 0.000 claims 1
- IJZYKTQNCMOUDY-UHFFFAOYSA-N 3-[[5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]methyl]-5-methyl-1,2,4-oxadiazole Chemical compound O1C(C)=NC(CN2N=C3C(N4CC(F)(F)CC4)=NC(=NC3=N2)C(C)(C)C)=N1 IJZYKTQNCMOUDY-UHFFFAOYSA-N 0.000 claims 1
- KPWOLGGHYKGHBQ-QMMMGPOBSA-N 3-[[7-(3,3-difluoropyrrolidin-1-yl)-5-[(2s)-1,1,1-trifluoropropan-2-yl]oxytriazolo[4,5-d]pyrimidin-2-yl]methyl]-4-methyl-1,2,5-oxadiazole Chemical compound C12=NN(CC=3C(=NON=3)C)N=C2N=C(O[C@@H](C)C(F)(F)F)N=C1N1CCC(F)(F)C1 KPWOLGGHYKGHBQ-QMMMGPOBSA-N 0.000 claims 1
- ZNGNMFUECOJYLB-UHFFFAOYSA-N 4-[5-tert-butyl-2-[(2-chloro-4-fluorophenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]morpholine Chemical compound C12=NN(CC=3C(=CC(F)=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCOCC1 ZNGNMFUECOJYLB-UHFFFAOYSA-N 0.000 claims 1
- YSNSJDCYGRXBCB-UHFFFAOYSA-N 5-[[5-tert-butyl-7-(3,3,4,4-tetrafluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-2-yl]methyl]-3-methyl-1,2,4-oxadiazole Chemical compound CC1=NOC(CN2N=C3C(N4CC(F)(F)C(F)(F)C4)=NC(=NC3=N2)C(C)(C)C)=N1 YSNSJDCYGRXBCB-UHFFFAOYSA-N 0.000 claims 1
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- ZIAHDNCQDKBFJT-ZETCQYMHSA-N 5-[[7-(3,3-difluoropyrrolidin-1-yl)-5-[(2s)-1,1,1-trifluoropropan-2-yl]oxytriazolo[4,5-d]pyrimidin-2-yl]methyl]-3-methyl-1,2,4-oxadiazole Chemical compound C12=NN(CC=3ON=C(C)N=3)N=C2N=C(O[C@@H](C)C(F)(F)F)N=C1N1CCC(F)(F)C1 ZIAHDNCQDKBFJT-ZETCQYMHSA-N 0.000 claims 1
- QTMULOFXQVEQOZ-UHFFFAOYSA-N 5-tert-butyl-2-[(1-cyclopropyltetrazol-5-yl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3N(N=NN=3)C3CC3)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 QTMULOFXQVEQOZ-UHFFFAOYSA-N 0.000 claims 1
- OUEZGUWLJNCYKB-UHFFFAOYSA-N 5-tert-butyl-2-[(1-methyltetrazol-5-yl)methyl]-7-(3,3,4,4-tetrafluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound CN1N=NN=C1CN1N=C2C(N3CC(F)(F)C(F)(F)C3)=NC(C(C)(C)C)=NC2=N1 OUEZGUWLJNCYKB-UHFFFAOYSA-N 0.000 claims 1
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- KFYXAUGVHGRNJG-UHFFFAOYSA-N 5-tert-butyl-2-[(2,3-dichlorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=C(Cl)C=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 KFYXAUGVHGRNJG-UHFFFAOYSA-N 0.000 claims 1
- WTPMJLIRUJCZKE-UHFFFAOYSA-N 5-tert-butyl-2-[(2,4-dichlorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC(Cl)=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 WTPMJLIRUJCZKE-UHFFFAOYSA-N 0.000 claims 1
- YOHLKYMCIJQBNG-UHFFFAOYSA-N 5-tert-butyl-2-[(2,4-dichloropyridin-3-yl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=NC=CC=3Cl)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 YOHLKYMCIJQBNG-UHFFFAOYSA-N 0.000 claims 1
- XSDHBGVRAUCFGF-UHFFFAOYSA-N 5-tert-butyl-2-[(2,5-dichlorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC=C(Cl)C=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 XSDHBGVRAUCFGF-UHFFFAOYSA-N 0.000 claims 1
- ODLWRQNWHFBTSI-UHFFFAOYSA-N 5-tert-butyl-2-[(2,5-dichloropyridin-3-yl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=NC=C(Cl)C=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 ODLWRQNWHFBTSI-UHFFFAOYSA-N 0.000 claims 1
- CAHVKHJFBYUOFB-UHFFFAOYSA-N 5-tert-butyl-2-[(2,6-dichloro-3-fluorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=C(F)C=CC=3Cl)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 CAHVKHJFBYUOFB-UHFFFAOYSA-N 0.000 claims 1
- JEEZVRNDVDBQQR-UHFFFAOYSA-N 5-tert-butyl-2-[(2,6-dichlorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC=CC=3Cl)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 JEEZVRNDVDBQQR-UHFFFAOYSA-N 0.000 claims 1
- FTYMKQUGMUDGPI-UHFFFAOYSA-N 5-tert-butyl-2-[(2-chloro-3,6-difluorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=C(F)C=CC=3F)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 FTYMKQUGMUDGPI-UHFFFAOYSA-N 0.000 claims 1
- PIIJYOOTXQTGOB-UHFFFAOYSA-N 5-tert-butyl-2-[(2-chloro-3-fluorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=C(F)C=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 PIIJYOOTXQTGOB-UHFFFAOYSA-N 0.000 claims 1
- QDUXQBXCTXYQBA-UHFFFAOYSA-N 5-tert-butyl-2-[(2-chloro-4,5-difluorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC(F)=C(F)C=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 QDUXQBXCTXYQBA-UHFFFAOYSA-N 0.000 claims 1
- OQKCKJXVYFXOFK-UHFFFAOYSA-N 5-tert-butyl-2-[(2-chloro-4-fluorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC(F)=CC=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 OQKCKJXVYFXOFK-UHFFFAOYSA-N 0.000 claims 1
- WFGGQTKEMSZZLT-UHFFFAOYSA-N 5-tert-butyl-2-[(2-chloro-5-fluorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC=C(F)C=3)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 WFGGQTKEMSZZLT-UHFFFAOYSA-N 0.000 claims 1
- QVSUOKOMRRWWLK-UHFFFAOYSA-N 5-tert-butyl-2-[(2-chloro-6-fluoro-3-methoxyphenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound COC1=CC=C(F)C(CN2N=C3C(N4CC(F)(F)CC4)=NC(=NC3=N2)C(C)(C)C)=C1Cl QVSUOKOMRRWWLK-UHFFFAOYSA-N 0.000 claims 1
- NTTJNHXSIRZMEP-UHFFFAOYSA-N 5-tert-butyl-2-[(2-chloro-6-fluorophenyl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidine Chemical compound C12=NN(CC=3C(=CC=CC=3F)Cl)N=C2N=C(C(C)(C)C)N=C1N1CCC(F)(F)C1 NTTJNHXSIRZMEP-UHFFFAOYSA-N 0.000 claims 1
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- DSRVMEDCLONMLH-FZMZJTMJSA-N n-[(3s)-1-[2-[[2-(trifluoromethyl)phenyl]methyl]-5-[(2s)-1,1,1-trifluoropropan-2-yl]oxytriazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-yl]acetamide Chemical compound C12=NN(CC=3C(=CC=CC=3)C(F)(F)F)N=C2N=C(O[C@@H](C)C(F)(F)F)N=C1N1CC[C@H](NC(C)=O)C1 DSRVMEDCLONMLH-FZMZJTMJSA-N 0.000 claims 1
- REFLCJJKBMMZKY-HNNXBMFYSA-N n-[(3s)-1-[5-(tert-butylamino)-2-[(2-chlorophenyl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-yl]acetamide Chemical compound C1[C@@H](NC(=O)C)CCN1C(C1=N2)=NC(NC(C)(C)C)=NC1=NN2CC1=CC=CC=C1Cl REFLCJJKBMMZKY-HNNXBMFYSA-N 0.000 claims 1
- KQGXVQRBRCEZII-UHFFFAOYSA-N n-tert-butyl-2-[(3-chloropyridin-2-yl)methyl]-7-(3,3-difluoropyrrolidin-1-yl)triazolo[4,5-d]pyrimidin-5-amine Chemical compound C12=NN(CC=3C(=CC=CN=3)Cl)N=C2N=C(NC(C)(C)C)N=C1N1CCC(F)(F)C1 KQGXVQRBRCEZII-UHFFFAOYSA-N 0.000 claims 1
- IDHQBMWIDCYCOA-UHFFFAOYSA-N n-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-2-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound CN1N=NN=C1CN1N=C2C(N3CC(F)(F)CC3)=NC(NC(C)(C)C)=NC2=N1 IDHQBMWIDCYCOA-UHFFFAOYSA-N 0.000 claims 1
- LDOJONMQHACGRZ-UHFFFAOYSA-N n-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-2-[(2-methylsulfonylphenyl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C12=NN(CC=3C(=CC=CC=3)S(C)(=O)=O)N=C2N=C(NC(C)(C)C)N=C1N1CCC(F)(F)C1 LDOJONMQHACGRZ-UHFFFAOYSA-N 0.000 claims 1
- MAPWAPPKSCYACG-UHFFFAOYSA-N n-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-2-[(4-methyl-1,2,5-oxadiazol-3-yl)methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound CC1=NON=C1CN1N=C2C(N3CC(F)(F)CC3)=NC(NC(C)(C)C)=NC2=N1 MAPWAPPKSCYACG-UHFFFAOYSA-N 0.000 claims 1
- DCESPOFJEOSECJ-UHFFFAOYSA-N n-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-2-[[2-(trifluoromethyl)phenyl]methyl]triazolo[4,5-d]pyrimidin-5-amine Chemical compound C12=NN(CC=3C(=CC=CC=3)C(F)(F)F)N=C2N=C(NC(C)(C)C)N=C1N1CCC(F)(F)C1 DCESPOFJEOSECJ-UHFFFAOYSA-N 0.000 claims 1
- 230000004770 neurodegeneration Effects 0.000 claims 1
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 1
- 125000005961 oxazepanyl group Chemical group 0.000 claims 1
- 125000004430 oxygen atom Chemical group O* 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000004193 piperazinyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 238000011321 prophylaxis Methods 0.000 claims 1
- 208000005069 pulmonary fibrosis Diseases 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 231100000241 scar Toxicity 0.000 claims 1
- 230000037387 scars Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 230000009885 systemic effect Effects 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000003831 tetrazolyl group Chemical group 0.000 claims 1
- 125000001984 thiazolidinyl group Chemical group 0.000 claims 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 1
- 201000010875 transient cerebral ischemia Diseases 0.000 claims 1
- 238000011282 treatment Methods 0.000 claims 1
- 125000001425 triazolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
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Landscapes
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11190777 | 2011-11-25 | ||
| PCT/EP2012/073315 WO2013076182A1 (en) | 2011-11-25 | 2012-11-22 | [1, 2, 3]triazolo [4, 5 -d] pyrimidine derivatives as agonists of the cannabinoid receptor 2 agonists |
| EP12794684.6A EP2782915B1 (en) | 2011-11-25 | 2012-11-22 | [1,2,3]TRIAZOLO[4,5-d]PYRIMIDINE DERIVATIVES AS AGONISTS OF THE CANNABINOID RECEPTOR 2 AGONISTS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20151423T1 true HRP20151423T1 (hr) | 2016-01-29 |
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| Application Number | Title | Priority Date | Filing Date |
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| HRP20151423TT HRP20151423T1 (hr) | 2011-11-25 | 2015-12-28 | DERIVATI [1,2,3]TRIAZOLO[4,5-d]PIRIMIDINA KAO AGONISTI RECEPTORA KANABINOIDA 2 |
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| EP (1) | EP2782915B1 (da) |
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| CN (1) | CN104039791B (da) |
| AR (1) | AR088970A1 (da) |
| AU (1) | AU2012342471B2 (da) |
| BR (1) | BR112014012479A2 (da) |
| CA (1) | CA2850697A1 (da) |
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| CO (1) | CO6930360A2 (da) |
| CR (1) | CR20140222A (da) |
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| MX (1) | MX346248B (da) |
| PE (1) | PE20141578A1 (da) |
| PL (1) | PL2782915T3 (da) |
| PT (1) | PT2782915E (da) |
| RS (1) | RS54319B1 (da) |
| SG (1) | SG11201402198XA (da) |
| SI (1) | SI2782915T1 (da) |
| TW (1) | TWI598350B (da) |
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| WO (1) | WO2013076182A1 (da) |
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| UA111640C2 (uk) * | 2011-11-08 | 2016-05-25 | Ф. Хоффманн-Ля Рош Аг | ПОХІДНІ [1,2,3]ТРИАЗОЛО[4,5-d]ПІРИМІДИНУ ЯК АГОНІСТИ КАНАБІНОЇДНОГО РЕЦЕПТОРА 2 |
| CN105555788B (zh) * | 2013-09-06 | 2018-11-23 | 豪夫迈·罗氏有限公司 | 三唑并[4，5-d]嘧啶衍生物 |
| EP3215506B1 (en) * | 2014-11-07 | 2019-01-02 | F.Hoffmann-La Roche Ag | Triazolo[4,5-d]pyrimidines as agonists of the cannabinoid receptor 2 |
| WO2017004133A1 (en) * | 2015-06-29 | 2017-01-05 | Nimbus Iris, Inc. | Irak inhibitors and uses thereof |
| EP3475283B1 (en) * | 2016-06-23 | 2021-08-11 | F. Hoffmann-La Roche AG | Novel[1,2,3]triazolo[4,5-d]pyrimidine derivatives |
| IL292015B2 (en) | 2016-06-23 | 2024-07-01 | Hoffmann La Roche | History of a [3,2,1]triazolo[5,4–D]pyrimidine with affinity for the type 2 cannabinoid receptor |
| CN109311886B (zh) | 2016-06-23 | 2021-11-09 | 豪夫迈·罗氏有限公司 | [1,2,3]三唑并[4,5-d]嘧啶衍生物 |
| EP3475280B1 (en) * | 2016-06-23 | 2020-04-08 | H. Hoffnabb-La Roche Ag | Novel [1,2,3]triazolo[4,5-d]pyrimidine derivatives |
| MX2020011501A (es) * | 2018-05-04 | 2020-12-07 | Inflazome Ltd | Compuestos novedosos. |
| CN112007156A (zh) * | 2019-05-30 | 2020-12-01 | 复旦大学 | 大麻素受体药物在制备治疗心肌细胞坏死性凋亡药剂中的应用 |
| CN112755189A (zh) * | 2019-11-02 | 2021-05-07 | 复旦大学 | 1型大麻素受体拮抗剂在制备治疗心肌细胞焦亡药剂中的应用 |
| EP4423087A1 (en) * | 2021-10-28 | 2024-09-04 | F. Hoffmann-La Roche AG | Synthesis of [1,2,3]triazolo[4,5-d]pyrimidines |
| CN115246832B (zh) * | 2022-06-15 | 2024-05-24 | 深圳湾实验室 | 一类去泛素化酶usp25和usp28靶向抑制剂及制备和应用 |
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| US2543333A (en) * | 1950-02-02 | 1951-02-27 | American Cyanamid Co | Derivatives of upsilon-triazolo (d) pyrimidine and methods of preparing the same |
| US4157443A (en) * | 1976-11-11 | 1979-06-05 | Ciba-Geigy Corporation | V-Triazolyl-[4,5-d]-pyrimidines |
| US20030139427A1 (en) | 2002-08-23 | 2003-07-24 | Osi Pharmaceuticals Inc. | Bicyclic pyrimidinyl derivatives and methods of use thereof |
| US7268133B2 (en) * | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
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- 2012-11-22 UA UAA201407119A patent/UA111643C2/uk unknown
- 2012-11-22 KR KR1020147013833A patent/KR20140097201A/ko not_active Application Discontinuation
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